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Biosynthesis of the Myxobacterial Antibiotic Corallopyronin A

  1. Özlem Erol 1,4,
  2. Till F. Schäberle  Dr.1,4,
  3. Alexander Schmitz1,
  4. Shwan Rachid Dr.2,
  5. Cristian Gurgui Dr.3,
  6. Mustafa El Omari1,
  7. Friederike Lohr1,
  8. Stefan Kehraus Dr.1,
  9. Jörn Piel Prof. Dr.3,
  10. Rolf Müller Prof. Dr.2,
  11. Gabriele M. König Prof. Dr.1

Article first published online: 25 MAY 2010

DOI: 10.1002/cbic.201000085

Issue

ChemBioChem

ChemBioChem

Volume 11, Issue 9, pages 1253–1265, June 14, 2010

Additional Information

How to Cite

Erol , Ö., Schäberle , T. F., Schmitz, A., Rachid, S., Gurgui, C., El Omari, M., Lohr, F., Kehraus, S., Piel, J., Müller, R. and König, G. M. (2010), Biosynthesis of the Myxobacterial Antibiotic Corallopyronin A. ChemBioChem, 11: 1253–1265. doi: 10.1002/cbic.201000085

Author Information

  1. 1

    Institute of Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn (Germany), Fax: +(49) 228-733250

  2. 2

    Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Center for Infection Research and Department of Pharmaceutical Biotechnology, Saarland University, P. O. Box 151150, 66041 Saarbrücken (Germany)

  3. 3

    Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany)

  4. 4

    These authors contributed equally to this work.

Publication History

  1. Issue published online: 7 JUN 2010
  2. Article first published online: 25 MAY 2010
  3. Manuscript Received: 11 FEB 2010

Funded by

  • Bundesministerium für Bildung und Forschung
  • DFG. Grant Number: FOR 845

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Keywords:

  • antibiotics;
  • biosynthesis;
  • Corallococcus coralloides;
  • corallopyronin A;
  • myxobacteria;
  • polyketides

Abstract

Corallopyronin A is a myxobacterial compound with potent antibacterial activity. Feeding experiments with labelled precursors resulted in the deduction of all biosynthetic building blocks for corallopyronin A and revealed an unusual feature of this metabolite: its biosynthesis from two chains, one solely PKS-derived and the other NRPS/PKS-derived. The starter molecule is believed to be carbonic acid or its monomethyl ester. The putative corallopyronin A biosynthetic gene cluster is a trans-AT-type mixed PKS/NRPS gene cluster, containing a β-branching cassette. Striking features of this gene cluster are a NRPS-like adenylation domain that is part of a PKS-type module and is believed to be responsible for glycine incorporation, as well as split modules with individual domains occurring on different genes. It is suggested that CorB is a trans-acting ketosynthase and it is proposed that it catalyses the Claisen condensation responsible for the interconnection of the two chains. Additionally, the stereochemistry of corallopyronin A was deduced by a combination of a modified Mosher's method and ozonolysis with subsequent chiral GC analyses.

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